Andrew Peacock/Courtesy Cookson Adventures

The 2020 Legend Awards

By The Editors on May 12, 2020

The 2020 Legend Awards are meant to serve as inspiration for future travel—when it is safe to do so. Learn more about this year’s awards on our methodology page.

When unparalleled luxury meets adventure, the limitations on travel nearly cease to exist. Bespoke travel companies are finding new, more high-end ways to explore the wonders of the world by land, sea, and air. From superyachts sailing toward the arctic to private jets hopping between far-flung destinations, these luxury tour curators bring their clientele the most authentic yet over-the-top experiences. 

Our Legend Awards honorees for best adventure experience each focus on a specific itinerary we love from our editors’ favorite tour companies of the year. These tour operators deliver five-star experiences in every destination they serve, but each has corners of the world they really shine in. Here are the best adventure experiences of the 2020 Legend Awards:

Cookson Adventures

Andrew Peacock/Courtesy Cookson Adventures

Cookson Adventures puts you on the frontlines of discovery with their chartered yacht experience to the Antarctic Peninsula. Cookson’s “polar experts” design the entire itinerary, and the expedition yacht is complete with a submersible and a helicopter, perfect for delving into uncharted territory.

Butterfield & Robinson

Sjoerd Vink/Courtesy Butterfield & Robinson

Butterfield & Robinson does terrific biking tours abroad, with a luxury flair and an average of 30 miles a day. We’re partial to their wine country biking itineraries, like their trip through Spain’s Wine Country in Rioja. The trip is a full sensory experience, as you ride through the rolling hills and gentle countryside, sampling tapas and wine along the way. 


Courtesy Roar Africa 

ROAR AFRICA is now offering “The Greatest Safari on Earth” for $125,000 per person. Set for 2021, 2022, and 2023, ROAR has partnered with Emirates to explore four of Africa’s iconic experiences and landmarks; visiting Victoria Falls and the Okavango Delta, witnessing the great migration in Kenya, and trekking to see the gorillas in Rwanda.

The Explorations Company

Courtesy The Explorations Company

The Explorations Company’s ultra-luxe itinerary is their extensive 16 Days Over Africa trip; it’s an Ultimate Air Safari Tour. The trip takes guests through Tanzania, Malawi, Zambia, Zimbabwe, and Botswana, allowing guests to see some of the most stunning wildlife in Africa. 

Abercrombie & Kent

Christian Knepper

Abercrombie & Kent’s Wings Over the World itineraries fly guests on private charters between destinations, so that you can visit the remote corners of the world without flying multiple legs over the course of 40 hours. Their Wings Over Argentina, Chile & Brazil Itinerary takes guests from Buenos Aires, through Patagonia and Torres Del Paine National Park in Chile, to Iguazu Falls in Brazil; a bucket-list trip, done up to the most lavish extent. 

Red Savannah

Helge Hansen/Courtesy Red Savannah

Experience all that Norway has to offer on Red Savannah’s Essence of Norway itinerary. This 11-day adventure will take you from Oslo to Norway’s fjordlands. Guests can enjoy a leisurely drive through the picturesque countryside, explore Oslo by bike, and head out on an adventure excursion like white water rafting.

Original Travel and Original Diving

Berenika L/Getty Images

Original Travel, a luxury tour operator and second-time Legend Awards honoree stole our hearts with their bespoke Egypt and Middle East itineraries. They’ve branched out to luxury diving tours in out-there destinations with Original Diving. Original Travel does two diving itineraries in Egypt: the Northern Red Sea, where travelers stay at the Arabian palace-inspired Four Seasons Resort Sharm El Sheikh, and the Southern Red Sea, where home base is The Oberoi Sahl Hasheesh beach resort. 


Childs Photos/Courtesy Tropicsurf

Active luxury isn’t just for bikers and hikers anymore. Tropicsurf offers curated surfing experiences, for first-timers or surf veterans. We’re particularly fond of Tropicsurf’s trip to Nihiwatu Sumba Resort in Indonesia. The Tropicsurf itinerary shows travelers the island’s majestic beauty through surfing, diving, and hiking. There’s also ample spa time built into the itinerary—balance is the Indonesian way, after all. 


Eric d’Herouville/Courtesy UNCOVR Travel

UNCOVR Travel offers super-luxe, one-of-a-kind trips while combating over-tourism by curating itineraries that primarily visit local, boutique businesses. The organization is Europe-focused, and we’re partial to their exploration of Portugal where guests explore the beauty of Lisbon and Porto, honing in on the stunning architecture, world-class wines, and local cuisine.

African Travel, Inc.

Iky’s Photographic/Courtesy Shamwari Game Reserve

African Travel, Inc. has been offering luxury tours in Africa for more than 40 years, bringing their guests to some of the most exclusive properties on the continent and sourcing the very best local guides. For a first visit to Africa, there are few things more perfect than their South Africa’s Natural Wonders itinerary, which begins in Cape Town, and concludes on safari with the Big Five with remote five-star glamping accomodations at Shamwari Private Game Reserve.

Leo Trippi

Yves Garneau/Courtesy Leo Trippi 

Leo Trippi does ski trips like no other, offering unprecedented luxury at some of the most iconic mountains around the world. Guests can choose between ski-in/ski-out chalets and tailored experiences for large groups, families, and honeymooners. We love their luxury catering experiences, where the Leo Trippi team organizes a private chef for your remote but over-the-top chalet. 

Scott Dunn 

Courtesy Scott Dunn

Scott Dunn brings guests to the wildest corners of the world—while bringing every possible luxury accoutrements with them. Their Iceland Northern Lights Experience starts with the vibrant culture in Reykjavik before heading to Southern Iceland to scout aurora borealis, hike across a glacier, and visit the waterfalls and geographic wonders that abound in this part of the world.